Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full bath. This is perfect for a multi generational family. The basement has plenty of storage and a dry, carpeted rec room with a wet bar and a half bath. The grounds feature mature landscaping and privacy. The roof, skylights, and gas fireplace are newer (installed in 2016). Home is on a private street with a cul-de-sac and is within walking distance to BCC and the state forest. Bosquet and Jiminy Pe

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and serenity.Second level has ample space with three guest bedrooms, two full baths and loft/office space open to the great room.The lower level walkout family room is gracious in size and has direct access to your private stone patio. Additionally, you have the fifth bedroom, full bath, laundry room and bonus storage room.Enjoy the association pool, Bousquet Mountain next door and all of the

Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a gracious entry with custom flooring and cedar hall closet that flows beautifully into the great room with vaulted ceilings, gas fireplace and glass doors to the screened porch and deck with a scenic view of the woods. The lovely updated kitchen is open to the dining area and great room for comfortable open common spaces. The primary bedroom has wood flooring, walk-in fitted closet and tastefully renovated en-suite bath with custom finishes. Included on the main level is the charming half bath, garage with storage and laundry room. The second floor features a large loft flex space with oversized closet, two guest bedrooms and stunning full bath. The lower level walkout is

Escape to an exceptional Post & Beam Berkshire Retreat nestled on the east side of Jiminy Peak Mountain Resort. Set on 25+ acres for seclusion and privacy, eat, play & live in this 4 bedroom, 2.5 bath chalet-style home with countless modern updates. Spectrum was recently added for everyday internet and tv streaming, as well as 5 new high-efficiency mini split air conditioning/heating units for those steamy Summer, and cold Winter, nights. New granite countertops and GE Cafe and Bosch stainless appliances in the recently refurbished kitchen are a true cook's delight. An open living concept, under a soaring 25 foot ceiling, creates multiple gathering spaces from the huge sectional to the plentiful island seating, and floor to ceiling dining room window frames the outdoors inside.

One of the largest condo units available @ 34 Bridge St. Just minutes from the movies, shopping and restaurants. Views facing east mountain to enjoy the sunrise. Beautiful morning light. Open floor plan with Juliette Balcony. Primary bedroom with private bathroom with double sinks. Both bedrooms include remote darkening shades. Stackable laundry and ac in unit. Includes plenty of storage with one dedicated parking spot. Come and enjoy easy living in town.

Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful surroundings. Conveniently located just minutes from Sheffield village, Canaan (CT), and Great Barrington, this versatile property works beautifully as a full-time residence, vacation retreat, or investment opportunity in the heart of the Berkshires. This is a new build, and taxes have not yet been determined.

Discover the perfect blend of comfort and charm with this stunning contemporary situated on two acres. There is a full-house Generac generator for comfort and peace of mind and central air. The great room is washed with natural light from the wall of windows and has a beautiful gas fireplace to provide additional warmth on cold Winter days. There is a circular flow into the spacious dining room and the updated kitchen making this home ideal for entertaining. A full bath and two charming guest bedrooms welcome visitors and offer opportunities for a home office. The oversized four-season sunroom offers magnificent light that takes in the picturesque landscaped surroundings and woodlands. It features an efficient gas stove for chillier days and screen inserts to help capture Summer breezes.

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved over this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring guest house featuring 3 bedrooms, 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends or caregiver

PANORAMIC VIEW, PRIVACY AND A STUNNING CONTEMPORARY is waiting to become your country sanctuary. As you drive up the long, private driveway, you feel your shoulders relax and then..peaceful thoughts take over as you soak in the sweeping south west view at the top of your private hill. The multi-level design of this home offers living with peace and tranquility for both gathering and quiet time alone, all while capturing the nature surrounding you on 5+ acres. Main level bedroom with private deck, full bath, office, cozy den and open kitchen/dining with direct access to the attached 3 car heated garage for convenience, dramatically opens to the Great Room in one direction and the primary bedroom with fireplace and newly designed luxurious ensuite bath with another guest bedroom and bath on

This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A beautiful heated swimming pool and a dedicated tennis court provide endless recreation. The expansive grounds, located at the end of a quiet road, guarantee unmatched privacy. Plus, a large solar array and new heating system drastically cuts utility costs. Enjoy total seclusion while being in the middle of everything that makes Great Barrington one of the most desirable towns in the Berkshires.

Berkshires Sanctuary - A Fully Renovated Retreat with Appalachian Trail Access & Nearby Three Mile Pond.Tucked away in a landscape of towering trees and rolling hills, this exquisite four-bedroom and three-bathroom, retreat has been reimagined with over $650,000 in premium renovations, offering the perfect balance of luxury and nature. With direct access to Appalachian trail and Three Mile Pond, just minutes away, this home is a haven for those who crave both serenity and adventure.Where Modern Elegance Meets Natural Beauty A Grand Welcome - A wraparound deck, inground pool, and upper balcony invite you to take in the forested surroundings, framed by black aluminum railings and Trex boards built for beauty and longevity.

A Stunning Three-Story Residence with Breathtaking Views for an Easy Care Lifestyle in the Berkshires.Majestic and magical perfectly describe this exquisite three-story mountain top home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either escape, join a quaint community or work at home with glorious views of the Berkshire Hills.Prime Location for Nature and Culture.Nestled in a charming small-town neighborhood, this home is bordered by beautiful woodlands, providing direct access to hiking trails and the nearby Appalachian Trail. Its central location places you at the heart of the area's vibrant culture and great outdoors.

Your waterfront lifestyle begins at this Hayes Pond sanctuary. From sunrise paddles to sunsets savored from the deck, this home is your private four-season escape in the Berkshires. The modern, open interior is designed to celebrate the water, with soaring cathedral ceilings and a wall of windows that frames the stunning lake view. A cozy wood stove, bright sunroom, and a large deck provide perfect spaces for relaxing or entertaining. This 4-bedroom retreat includes a primary suite featuring a calming soaking tub. Your private, grassy shoreline is your personal gateway to the lake--perfect for launching kayaks, fishing, swimming, or the occasional bonfire. This is the ultimate waterfront escape, where every detail is focused on a life lived by the water.

ICONIC VICTORIAN IN SUPERB LOCATIONThis stunning residence is just a stone's throw from the renowned Clark Art institute withs its internationally revered collection of the art of Renoir, Monet, Degas, Sargent, Homer, Remington, Inness and Cassatt (among many, many others), and its expansive 140 acre campus full of trails wandering through meadows and woodlands. Built in 1888 by Archibald Hopkins, son of Williams College President Mark Hopkins, the incomparable home shares a spacious two thirds of an acre with wonderful gardens, handsome Goshen stone walls and two lovely pergolas. The gracious entry hall, distinguished by a dramatic stairway with soaring leaded glass windows, leads to elegant living and dining rooms, and a warm bookshelf-lined library. All have French doors opening to

Once the First Methodist Episcopal Church, built in 1898, this incredible 6,500 sq ft property has been thoughtfully reimagined as a two-family residence and offers unparalleled potential for an artist's dream live/work space. Located just a short walk from downtown on a 3/4 lot abutting an 18 acre nature reserve, this building is ideally positioned to offer both the tranquility of the Berkshires and proximity to its cultural and natural attractions.On one side, the 4,000 sq ft SoHo-style loft spans two levels, blending historic charm with modern luxury. With soaring ceilings, original exposed wood beams, and rich hardwood floors, this 4-bedroom, 5-bath residence provides spacious, light-filled living areas w/ cozy floating sitting nooks that overlook the expansive great room below.

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming gazebo and a generous deck, perfect for hosting gatherings or relaxing in your own outdoor oasis.The oversized garage provides ample storage and includes a versatile space above, ready for your expansion ideas. With rough plumbing and electrical already in place, customizing this area is effortless. Located 2 min from Monument Mountain Reservation and 6 min to Main Street.

Welcome to a rare waterfront oasis offering over 650 feet of private frontage on the deepest part of Hayes Pond. Your private dock and beach area provide direct access to swimming, kayaking, and fishing, while a perfectly positioned gazebo is ideal for entertaining by the water. Inside, breathtaking water views grace every room through expansive windows. The open-concept design flows seamlessly from the great room to wrap-around decks, blurring the line between indoor and outdoor living. Cathedral hardwood ceilings and beautiful wood floors create an atmosphere of inviting warmth, anchored by a custom tile hearth and wood stove that serves as a stunning focal point. Retreat to the spacious primary suite, complete with its own cozy wood stove and a private en-suite bathroom.

Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires.Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind.

Updated and spacious condo just a short distance from Main Street Stockbridge, downtown Lenox, and all the Berkshires has to offer! Premier Unit at Stockbridge Terrace: Enjoy peaceful living on a private cul-de-sac with a limited number of units. The main level living setup is perfect for the primary resident, featuring a large primary bedroom with an en-suite bath and walk-in closet, an open-concept kitchen that has been recently updated complete with top-of-the-line appliances and all new high end cabinetry. The Great Room boasts cathedral ceilings bringing an abundance of natural light and a soaring gas fireplace for added ambiance. Enjoy your private backyard views from the 4-season sun porch equipped with both heat and A/C for year-round comfort.

Loft 402 is one of Greylock WORKS' most sought-after residences: a large, south-facing 2BR | 2BA + Study Berkshires loft with soaring 16-foot ceilings, luminous all-day light, and sweeping views of the hills. Set within the region's most celebrated mill conversion, this exceptional home blends architectural authenticity with contemporary design in a way that defines modern Berkshire living.The expansive living and dining area features regionally sourced schist countertops, gorgeously restored original hardwood floors, and hand-burnished structural elements that anchor the home in its mill history. South-facing windows flood the space with natural light and frame tranquil hill views that shift with each season.